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Chemistry Equations - Unit 4 (Organic)

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  1. SN1 and SN2
    • SN1: rate = k[halogenoalkane]1x[nucleophile]0
    • SN2: rate = k[halogenoalkane]1x[nuclephile]1
  2. Preparation of aldehyde
    CH3CH2OH + [O] → CH3CHO +H2O
  3. Preparation of ketone
    CH3CH(OH)CH3 + [O] → CH3COCH3 + H2O
  4. Nucleophilic addition
    • Aldehydes:
    • nucleophilic_addition
    • Racemic mixture formed due to trigonal planar.
    • Ketones:
    • Same but two no H on carbon.
  5. Hydrolysing hydroxynitriles
    • chart?chf=bg,s,00000000&cht=tx&chl=CH_3CH(OH)CN%20%2B%202H_2O%2B%20H%5E%2B&chs=514x44→ chart?chf=bg,s,00000000&cht=tx&chl=CH_3CH(OH)COOH%20%2B%20NH_4%5E%2B&chs=472x44
    • Heat under reflux, with dilute acid
    • Racemic mixture of 2 enantiomers
  6. Reduction of hydroxynitriles
    • chart?chf=bg,s,00000000&cht=tx&chl=CH_3CH(OH)CN%20%2B4%5BH%5D&chs=404x40→ chart?chf=bg,s,00000000&cht=tx&chl=CH_3CH(OH)CH_2NH_2&chs=376x38
    • Produces a hydroxyamine
  7. Reduction of aldehyde
    • chart?chf=bg,s,00000000&cht=tx&chl=CH_3CHO%20%2B%202%5BH%5D%20%5Crigh%20CH_3CH_2OH&chs=550x40
    • Use LiH4Al in dry ether, room temperature
  8. Reduction of ketone
    • chart?chf=bg,s,00000000&cht=tx&chl=CH_3COCH_3%20%2B%202%5BH%5D%20%5Cright%20CH_3CH(OH)CH_3&chs=684x40
    • Use LiH4Al in dry ether, room temperature
  9. 2,4 Dinitrophenylhydrazine and carbonyl compound
    dnpproduct1

    Yellow/orange ppt if carbonyl compound
  10. Oxidation of aldehyde
    • chart?chf=bg,s,00000000&cht=tx&chl=CH_3CHO%20%2B%5BO%5D%20%5Crigh%20CH_3COOH&chs=498x40
    • Either use Feelings and warm - red Cu2O ppt
    • Or use Tollen's and warm - silver mirror
  11. Iodoform reaction
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COR%20%2B%203I_2%20%2B4NaOH&chs=416x36→ chart?chf=bg,s,00000000&cht=tx&chl=CHI_3%20%2B%20RCOONa%20%2B%203NaI%2B3H_2O&chs=548x36

    • Yellow ppt if positive
    • Tests positive for methyl ketone (CH3CO) and methyl alcohol (CH3CH(OH))
  12. Preparation of carboxylic acid (oxidation of alcohol)
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3CH_2OH%20%2B2%5BO%5D&chs=326x40→ chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%20%2BH_2O&chs=306x36

    potassium dichromate, sulphuric acid, reflux
  13. Hydrolysis of nitriles
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3CN%20%2B2H_2O%2BHCl&chs=374x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%2BNH_4Cl&chs=352x36

    dilute acid, reflux
  14. Carboxylic acids with water and NaOH
    • chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%2BNaOH&chs=340x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3COONa%20%2BH_2O&chs=324x36
    • chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%20%2BH_2O&chs=306x36⇌chart?chf=bg,s,00000000&cht=tx&chl=CH_3COO%5E-%2BH_3O%5E%2B&chs=314x42
  15. Reduction of carboxylic acid
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%20%2B%204%5BH%5D&chs=308x40→chart?chf=bg,s,00000000&cht=tx&chl=CH_3CH_2OH%2BH_2O&chs=330x36

    LiH4Al, dry ether
  16. Carboxylic acid and carbonates/hydrogen carbonates
    • chart?chf=bg,s,00000000&cht=tx&chl=2CH_3COOH%2BNa_2CO_3&chs=384x38→chart?chf=bg,s,00000000&cht=tx&chl=2CH_3COONa%2BCO_2%2BH_2O&chs=436x36
    • chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%2BNaHCO_3&chs=374x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3COONa%2BCO_2%2BH_2O&chs=420x36
  17. Carboxylic acids and PCl5
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%2BPCl_5&chs=306x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3COCl%20%2BPOCl_3%2BHCl&chs=418x36

    Room temperature
  18. Esterification
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%2BC_2H_5OH&chs=368x36⇌chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOC_2H_5%2BH_2O&chs=354x36

    with conc. sulphuric acid in water bath, then pour into dilute NaHCO3 

    or under reflux with conc sulphuric acid

    chart?chf=bg,s,00000000&cht=tx&chl=C_2H_5OH%2BCH_3COCl&chs=348x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOC_2H_5%2BHCl&chs=348x36


    higher yield because not reversible
  19. Carboxylic acids and Cl2
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3CH_2COOH%2BCl_2&chs=356x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3CHClCOOH%2BHCl&chs=396x36

    UV light, free-radical substitution
  20. Acid Hydrolysis
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOC_2H_5%2BH_2O&chs=354x36⇌chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%2BC_2H_5OH&chs=368x36


    • Conditions: dilute acid (H+(aq) catalyst), reflux
    • Low yield due to reversible reaction
  21. Alkaline Hydrolysis
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOC_2H_5%2BNaOH&chs=386x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3COONa%2BC_2H_5OH&chs=386x36

    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COONa%2BHCl&chs=318x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%2BNaCl&chs=318x36


    This reaction is used to make soaps
  22. Transesterification
    • Ester + another acid
    • chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOC_2H_5%2BHCOOH&chs=422x36⇌chart?chf=bg,s,00000000&cht=tx&chl=HCOOC_2H_5%2BCH_3COOH&chs=422x36

    Used to make low fat margarine

    • Ester + another alcohol
    • chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOC_2H_5%2BCH_3OH&chs=414x36⇌chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOCH_3%2BC_2H_5OH&chs=412x36

    Used to make biodiesel
  23. Polyesters
    • Condensation polymerisation - small molecule is lost
    • 2000px-PET_by_Polycondensation_V1.svg
    • Used to make fine threads in synthetic fibres
  24. Preparation of acyl chlorides
    chart?chf=bg,s,00000000&cht=tx&chl=3CH_3COOH%2BPCl_3&chs=326x36→chart?chf=bg,s,00000000&cht=tx&chl=3CH_3COCl%2BH_3PO_3&chs=338x36

    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%2BSOCl_2&chs=328x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3COCl%2BSO_2%2BHCl&chs=370x36


    +Reaction of carboxylic acid with PCl5
  25. Acyl chlorides and water
    • chart?chf=bg,s,00000000&cht=tx&chl=CH_3COCl%2BH_2O&chs=284x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOH%2BHCl&chs=300x36
    • waterm1.GIF
    • waterm2.GIF
    • waterm3.GIF
  26. Acyl chloride and alcohols
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COCl%2BCH_3OH&chs=346x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3COOCH_3%2BHCl&chs=344x36


    • Room temperature, 100% yield, easy to separate products
    • Expensive to make acyl chlorides, toxic HCl given off
  27. Acyl chloride and ammonia
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COCl%2BNH_3&chs=290x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3CONH_2%2BHCl&chs=322x36


    makes an amide

    • with excess ammonia, white smoke of NH4Cl forms
    • chart?chf=bg,s,00000000&cht=tx&chl=HCl%2BNH_3%5Crigh%20NH_4Cl&chs=358x36
  28. Acyl chloride + amines
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COCl%2BCH_3NH_2&chs=368x36→chart?chf=bg,s,00000000&cht=tx&chl=CH_3CONHCH_3%2BHCl&chs=382x36

    makes N-substituted amide
  29. Reduction of acyl chlorides
    chart?chf=bg,s,00000000&cht=tx&chl=CH_3COCl%2B4%5BH%5D&chs=286x40→chart?chf=bg,s,00000000&cht=tx&chl=CH_3CH_2OH%2BHCl&chs=324x36


    add LiAlH4 and dry ether
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Author
valentinafunaro
ID
317105
Card Set
Chemistry Equations - Unit 4 (Organic)
Description
chemistry
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